


The One With The Cock Ring

by HolyFuckingHell



Series: Dean's Drawer [6]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Castiel/Top Dean Winchester, Bottom!Cas, Cock Rings, Destiel - Freeform, Established Castiel/Dean Winchester, Established Relationship, Fluff, Fluff and Smut, Fucking, M/M, Sex Toys, Smut, top!dean
Language: English
Status: Completed
Published: 2020-02-10
Updated: 2020-02-10
Packaged: 2021-02-28 00:14:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,615
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22644691
Author URL: https://archiveofourown.org/users/HolyFuckingHell/pseuds/HolyFuckingHell
Summary: The random thing selected from Dean's wonderfull sex drawer this time is a cock ring. “This will make you last longer, right?”
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Series: Dean's Drawer [6]
Series URL: https://archiveofourown.org/series/1569292
Comments: 7
Kudos: 135





	The One With The Cock Ring

**Author's Note:**

> This one took me a while to get up here and I'm sorry about that. I wish I had a great excuse. Anyway, this was really fun to write, I hope y'all like it! Part six!!!

“Are they leaving?” Cas asks Dean, meeting him in the hallway.

“Yup,” Dean answers as they walk towards his room, “It’s easy getting Sam out of the bunker, but hard to get Jack to go with him.”

“What did you tell them?” Cas asks curiously, linking their elbows together as they walk like old couples do while strolling sweetly through the park.

The elbow thing is new to Dean, Cas has never done that before. But it makes sense that he would so he doesn’t think much of it. “Uhh, they’re gonna go on a food run,” Dean explains, “Sam said if they’re going now, then we have to go on the next errand though.”

“We?” Cas asks. They stop right outside Dean’s door. “Sam said you an I?”

“Well, he said  _ I _ have to, but you’re coming with me right?” Dean says looking into Cas’s eyes with a lost puppy expression.

“Of course,” Cas says plainly.

“Okay,” Dean turns the handle and swings the door open, crashing his and Cas’s lips together needily. They kiss breathlessly, fumbling over to the bed. Dean lays back and pulls Cas down with him, laying at the edge with his legs dangling off. Dean grinds his hips up into Cas and Cas climbs off of Dean. “What?” Dean asks confused, did he do something wrong?

“Take off your clothes,” Cas says, taking off his coat and loosening his tie. Cas gets undressed pretty quickly, all he’s wearing now is his underwear and his dress shirt that is unbuttoned and open. He puts his hand on the handle of the drawer, “Is there anything in here you want to use  _ specifically _ ?” 

Dean shakes his head, pulling off his shirt, only wearing his boxers now. “Anything…” 

“So pick random again, Dean?” 

“Yeah sure,” Dean says scooting up on the bed. Cas reaches in blindly and pulls out lube. Cas looks from it to Dean like he isn’t sure what to do now. “Go again,” Dean says obviously and reassuring Cas. Cas sets the lube on top of the table and reaches in again, this time pulling out a thin, blue ring. 

Cas smiles, “This will make you last longer, right?” 

Dean looks at Cas with a blank expression, throwing his hands up. “Really, dude?”

“Sorry,” Cas says.

“Well,” Dean sighs, “That’s the idea.”

“Okay,” Cas picks the lube back up and crawls onto the bed kneeling by Dean. Without a word, Cas pulls Dean’s underwear down and puts lube around his dick, stroking gently. He then puts lube around the inside of the ring, when he looks back down at Dean he sighs heavily, “Dean, you can’t be erect when I put this on you.”

Dean blinks and shakes his head dramatically, “Dude, you just  _ literally _ jacked me. What did you expect?” Dean laughs.

Cas tilts his head, slumping his shoulders, “Obviously I expected you to ‘keep it down’ until I got the ring on you.” Cas says with one hand doing air quotes. 

Dean rolls his eyes and really focuses on the most unarousing things he can think of until Cas can put the ring on. “Better?” Dean says grumpily and slightly embarrassed.

Cas gives a small nod, holding him in one hand and reaching down to put the ring on with the other. Cas gets pretty close to Dean’s dick with the ring before pulling it away, “Dean focus!”

“I’m sorry!” Dean yells back.

“I can’t even touch you, Dean?” Cas lets go, “It’ll only take a second! You need to stay soft for  _ just one second. _ ”

“Cas you’re all too-” Dean looks Cas up and down, biting the side of his lower lip before saying, “Maybe I should just do it.”

“Fine,” Cas exhales calmly, handing Dean the ring so he can handle it himself. 

Dean takes it from him and looks down at it, focusing intently. A few seconds go by and nothing happens. Almost a full minute goes by, and still, nothing happens. “Cas,” Dean covers his face with his free hand out of sheer embarrassment, “Go stand over there or something.”

Cas looks at his eyes as Dean uncovers them and says in disbelief, “Are you serious?” Dean nods so Cas begrudgingly gets off the bed and stands on the other side of the room. 

“Actually Cas,” Dean says shutting his eyes tightly, “Go stand in the hallway.”

Cas starts walking to the door grumbling lowly, “Dean, this is getting ridiculous.”

Luckily for Dean, when Cas walks out it is much easier to relax and put the ring on. He calls Cas back into the room and Cas practically pounces on the bed when he walks through the door. 

“Finally,” Cas says pulling his underwear off and putting lube onto three of his fingers. “I like that I drive you crazy, Dean.”

Dean watches Cas slide two fingers effortlessly into himself, “Yeah I like it too,” He says back slowly.

“You are remarkably easy,” Cas says with a grin.

“Alright Cas, I get it.” Cas slides a third finger in, this time with a soft hum. Dean feels,  _ how can he put this _ , harder than usual? Yeah, that seems about accurate. 

Dean climbs up over Cas and Cas takes his fingers out. “You look so good Dean,” Cas says staring into Dean’s eyes, “I think I’m ready.”

“Why are you rushing, Cas?” Dean asks, turning his head sideways.

“I am not  _ rushing. _ ”

“Cas,  _ you are rushing, _ why?”

Cas makes a scrunched up face and looks down at Dean’s dick, “You aren’t supposed to wear that for very long,” Cas says with a grimace. 

“What?” Dean says concerned, “Is this dangerous? Is my dick gonna be okay? Fuck.”

Cas laughs “Your  _ ‘dick’ _ is fine, Dean,” Cas shakes his head, “You are going to be fine, I just figured why waste time? Now let’s go, I am ready.”

Dean leans back, kneeling between Cas’s open legs. “No way,” Dean shakes his head, “That was too quick, you aren’t ready.”

Cas raises an eyebrow at Dean with a straight face. Seconds later, Cas’s eyes start glowing bright blue, the bright increasing slowly for a few moments and then they go out, back to Cas’s normal, beautiful blue eyes. “Alright, I am definitely ready now, Dean.” Cas spreads his legs a little farther and lifts his hips off the bed a little higher.

Dean holds around Cas’s waist and starts to line up, “Oh Cas, taking the easy way instead of the fun way,” Dean smirks.

Cas glides a finger over Dean’s lower stomach before letting his arm fall to the bed, simply because Cas just likes to touch him, “Trust me, Dean, this is  _ still _ the fun way.” Dean smiles and slides gently into Cas. “Oh…” Cas hums lowly again, closing his eyes, “That feels good.”

“Yeah?” Dean asks but also agrees.

“Yeah,” Cas says biting his lip. Dean moves slowly out and in, resulting in more low hums and faint grunts from Cas. “Faster please,” Cas says politely like he’s asking, but means like he’s telling. Dean speeds up slightly. 

“Ugh, Cas,” Dean grunts. Dean thinks it’s a little odd that at the beginning of their relationship… Well their  _ sexual _ relationship, Cas was willing and happy to be the one being fucked. That was until Dean realized that he liked it too, then Cas was the one fucking  _ him. _ Then somehow after all this time, Cas had been kinda… Scared? To do it again. But he got over that  _ insanely quickly _ and now is completely and totally fine with it all over again. And now he’s asking Dean to move faster. Heh. Odd guy.

“Dean,” Cas pauses, clenching and jerking forward at Dean’s sudden change of angle, “Hmm…” Cas hums low and drawn.

“Fuck, Cas!” Dean has never understood how Cas could be so warm. Dean moans again, thrusting harder for a time or two. He is always  _ so fricken’ warm _ . It’s humanly impossible. 

Oh, duh. He’s an angel. Dean is fucking an angel. That seems to slip his mind quite often. Which is why Dean is so close to finishing and why it seems like Cas is…  _ not. _

Dean tries to say something but no words come out, just a wimpy moan. He tries again, “Cas,” Dean breaks for an unexpected sharp inhale in, “Gettin’ close.”

Cas reaches for his own cock and begins stroking it slowly, “Alright, keep going,” Cas acknowledges. 

Dean keeps thrusting fast like Cas had wanted him to, but slowly loses any rhythm he previously had the closer he gets. He can’t  _ not _ think about how warm Cas is, or how tight he is, or how soft, or slick! Goddamnit! He feels so good. And he looks so good. Cas speeds up his hand that’s on his dick and jacks harder. Dean can’t take it.

Cas looks up at Dean, looking him right in the eyes. Admiring deeply. “Cas, I-” Dean can’t finish what he’s going to say because he’s interrupted by a moan.

“I know,” Cas says kind of roughly, giving Dean a dorky grin. Dean twists his face in a lame attempt to smile though he’s losing control. “Dean…” Cas pants, “Come.”

Dean’s chin tilts up as he comes deep into Cas. He watches Cas as he pulls a hand into his hair, pushing it back before finally holding on tightly to the hair behind his head. Dean has never seen Cas do that before. Dean’s eyes shut tightly as he is thrown into orgasm. 

Cas screams. Or maybe it was Dean? Dean can’t tell. Maybe it was both of them? Dean attempts to continue thrusting into Cas but is very unsteady. Dean opens his eyes and sees the come on him before he feels it, It has to be Cas’s come. Did Cas come with Dean? He must have. Next, he sees Cas laying with both his arms outstretched to the sides and his chest heaving. 

Dean gently slides out of Cas and slowly moves to lay down beside him. Wordlessly, Dean curls up into Cas’s body, shaking slightly, laying his head on Cas’s chest since the pillows are at the other end of the bed.

Cas smiles hugely at Dean, “Wow,” He says with an excited voice. He reaches over for Dean’s dick and effortlessly slides the ring off. “Wow!” 

“What?” Dean asks feeling a little nervous.

“Dean you were- Wow!” Cas can’t seem to spit out what he’s trying to say.

“Huh?” Dean asks sitting up a little to look at Cas. Cas grabs the sides of Dean’s face and pulls him in for a sloppy kiss. Dean gives in immediately, opening his mouth slightly so that Cas can glide his tongue over his own. 

Cas pulls away and lets his head fall back onto the bed, leaving Dean still sitting up a little bit, looking at Cas, wondering what the hell he’s talking about. 

Cas is still smiling a huge cheesy smile that Dean doesn’t often see. “Dean you were so amazing,” Cas starts rubbing his hand over Dean’s arm as he talks, “You felt  _ so good. _ You were  _ way _ harder, or firmer than usual, wow. And you lasted much longer as well.” 

Dean gives a slight chuckle, covering his slight embarrassment and awkward feeling he has from Cas’s bizarre description of what just happened. Dean lays his head back on Cas’s chest not saying anything. He wouldn’t even really know what to say. 

“I felt  _ amazing! _ ” Cas practically yells. Dean hasn’t seen Cas this excited in maybe forever. The guys acting like a puppy. “Dean, you were amazing!” Dean starts blushing furiously, still unable to speak, really just trying to process what Cas is saying. “I don’t think, that in all of the porn I’ve seen, that they did an accurate job of depicting how good that actually feels if your partner wears a penis ring.”

“Cock,” Dean mumbles, correcting Cas, though he regrets it instantly. 

“What?” Cas asks confused. He  _ did _ hear Dean, he just doesn’t understand. 

“It’s not a  _ penis _ ring it’s called a co- nevermind,” Dean sighs, “Of course it wasn’t accurate,” Dean says, “Porn isn’t real, Cas.”

“I know Dean,” Cas laughs, “Otherwise the bottom would have screamed as loud as I did.”

“That scream was you?” Dean asks.

“The second one was me. The first one was you,” Cas clears up, “You came so hard, Dean. You know how I don’t usually scream. But it felt so good, Dean!” Cas will not stop saying Dean’s name, but Dean thinks it’s cute how excited he is. 

Dean thinks back, “Did you say I was ‘firmer?’”

“Yes,” Cas answers, moving his roaming hand around to Dean’s middle back, gently grazing his fingers over him. 

“Yeah, that’s kinda how it felt.”

“Oh!” Cas jumps with excitement, making Dean jump in shock, “How  _ did _ it feel?”

Dean thinks, “Well, I definitely felt harder…” Dean nuzzles his head into Cas, trying to get more comfortable. He knows Cas won’t judge him or be rude about anything he says, but he still feels just a bit  _ uncomfortable _ . “It also was like- I felt kinda- It was like I was 10x more sensitive, it felt really good. And it sorta felt like, you know like the build-up, like I was on the edge the entire time. You think I um,” Dean swallows, “You think I like, lasted longer?”

“Um, yeah.” Cas answers like it's obvious, “You did last longer. And you ejaculated longer too.”

Dean shuts his eyes tight, “Thanks, Cas.” 

“Dean,” Cas starts, “You don’t have to feel unnatural about this.” Cas squeezes Dean like a quick hug. “How was your orgasm, Dean?” This is not the first time Cas has asked Dean about his orgasm. When they first started doing the dew, Cas would ask Dean almost every time about how his orgasm was. ‘Was it satisfactory?’ ‘Did it feel gratifying?’ or ‘Was the orgasm adequate?’

“It was very intense, Cas,” Dean says trying not to be too begrudging. “I think it may have also lasted longer as well.”

“Really?” Cas asks in aw. “More intense like how?”

How is Dean supposed to explain this? He thinks before saying “Like a mind-shattering surge, I don’t know… how to… explain it.”

Cas replies softly, “Okay,” A few moments pass by before Cas says something, louder this time. “I want to try it.”

Dean blinks, “Right now?” He sits up all the way to see Cas’s face. Cas is still laying with his arms stretched out, now that one arm isn’t wrapped around Dean anymore. “Cas, I don’t know if I can-”

“Not yet,” Cas says looking straight up at the ceiling. “I know I have what you call ‘that crazy angel stamina,’ but I meant after your refractory.”

“My what?” Dean asks baffled. 

“Your refractory period. The time after orgasm that no matter how hard you try, you can’t get erect again. You should be fine in maybe 15 minutes, maybe sooner.”

Dean turns his head at Cas with a relaxed smile as Cas looks up at him. He looks into Cas’s eyes for a moment before finally saying, “Cas, I love you.” 

Almost no time passes before Cas says “I know.”

“What?”

“I know you love me, Dean. For one thing, I wasn’t fully undressed, and you made me leave the room so you could ‘go soft.’ That’s not libido anymore, Dean, that’s love.”

Dean looks away, suddenly feeling unsure, “Cas, I don’t just love you for sex.”

Cas laughs and sits up finally, “I know Dean, that was just one reason.”

Dean looks back at Cas, “Oh.”

“You said it twice,” Cas teases. Dean shoots him a grumpy look, “I love you too.”

**Author's Note:**

> Please leave comments! They honestly make my day and I love hearing what y'all have to say!


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